Triethylamine → 2,3,6-Trifluoropyridin-4-amine

HRID 272686Notes

Reaction equation

HRID 272686 reaction equation
Cl[C:2]1[C:3]([F:11])=[N:4][C:5]([F:10])=[C:6]([F:9])[C:7]=1[NH2:8].CCN(CC)CC.[H][H]>CO.[Pd]>[F:10][C:5]1[C:6]([F:9])=[C:7]([NH2:8])[CH:2]=[C:3]([F:11])[N:4]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 34881444-Amino-3-chloro-2,5,6-trifluoro-pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 139996122,3,6-Trifluoropyridin-4-amineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-chloro-2,5,6-trifluoro-pyridin-4-ylamine (1.82 g, 10 mmol), 5% Pd/C (0.5 g), and Et3N (3.04 g, 30 mmol) in 50 mL of MeOH was equipped with a balloon of hydrogen gas and stirred at room temperature overnight. The solution was filtered through diatomaceous earth (Celite®). The filtrate was concentrated under vacuum and the residue was partitioned between ethyl acetate and H2O. The aqueous layer was extracted with additional ethyl acetate, and the combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel with 7:3 hexanes/ethyl acetate to provide 1.33 g (90%) of the desired product. MS (DCI) m/e 149 (M+H)+.

Workup

  1. filtrationThe solution was filtered through diatomaceous earth (Celite®)
  2. concentrationThe filtrate was concentrated under vacuum
  3. customthe residue was partitioned between ethyl acetate and H2O
  4. extractionThe aqueous layer was extracted with additional ethyl acetate
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by flash column chromatography on silica gel with 7:3 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-d489b0a642c0457caf2247a48c2d0bf2
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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